Chelsea Boots Men

The Boots That Every Single Man Should Have In His Closet

This article was originally published by AskMen UK — so don't mind the references to things like "pounds," "chaps" and "packets of crisps," whatever those are.

I’d be happy to bet good money that a Chelsea boot will never be “wrong” but solid proof comes from the designers who continue to reimagine this smart-casual staple season after season. For spring/summer 2016, the menswear catwalks might have been dominated by dandy-ish loafers or sporty plimsolls but that’s not to say that a classic Chelsea boot didn’t make an appearance; at Christopher Kane they came highly polished and styled with tailored shorts, while Paul Smith paired black versions with shimmery suits and bold yellow or white interpretations with more traditional grey tailoring. At Sandro – which has become renowned for wearable yet directional collections by Ilan Chetrite – brown Chelsea boots accompanied navy slacks (and yes, it worked) and black versions gave a smart spin to denim.

Bethan Holt is the fashion features editor at The Telegraph in the UK.

Why they’re timeless:

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First invented during the Victorian era as a practical walking boot (the elasticated side panels added much-sought after flexibility to stiff leather), the Chelsea boot gained true fashion kudos in the '60s when they became the shoe of choice for The Beatles and The Rolling Stones. In many ways, those two bands’ contrasting looks – but mutual love for the same boot style – typifies why Chelsea boots are such a useful wardrobe tool. McCartney, Lennon and co’s slim-fit tailoring, skinny ties and buttoned-up shirts were complemented nicely by a shiny pair, but equally, a more bashed-in Chelsea boot was great with The Rolling Stones’ signature leather jackets, jeans and skinny tees. And 50 years on, there’s no style shame in channelling a Beatle or a Rolling Stone.

What to look out for:

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The defining characteristics of a Chelsea boot include elasticated side panels, a distinctive tab and a round-ish toe. While there are no hard-and-fast rules, it’s generally best to find a pair which fit snugly around your ankle to give that sleek silhouette, especially if they come up over the ankle bone.

How to wear them:

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The biggest point of contention when it comes to Chelsea boot styling is whether they can be worn with a suit. Our advice? It’s all about how they work with your trousers of choice. At 2014's Brit awards, Labyrinth finished his floral suit with a pair of black Chelsea boots which worked just fine because the meeting point looked neat. But if the tab is going to stick out from under the trousers or cause rumpling then stick to brogues and socks instead.

Chelsea boots are a brilliant way to smarten up jeans, which you should roll up a bit to show off your boot to its full potential. At Saint Laurent, Hedi Slimane has brought back Chelsea boots with a cubana heel; they’re a modern classic which look amazing when worn with skinny-ish jeans and a leather jacket, but these are not one for the office.

If you’re just starting on with a Chelsea boot then check out Church’s for more formal versions, or Clarks if it’s all about finding a new rough-and-ready weekend go-to.